By B. J. Wakefield (Auth.)
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Example text
1 . Competition with metallation m a y b e illustrated by one of the earliest examples. The reactions involved are as follows: (6) Br Li Br J C a u t i o n should be used w h e n e m p l o y i n g T M E D A as a promoter for m e t a l - h a l o g e n e x c h a n g e reactions, since it evidently accelerates metallation m o r e than m e t a l - h a l o g e n e x c h a n g e / 1 8 7 1 0 54 The Chemistry of Organolithium Compounds Metal-halogen exchange [eqn. -anisyl-lithium are obtained. However, when the reaction is carried out at higher temperatures or for longer times, metallation [eqns.
The disadvantage of the slowness of the reactions in hydrocarbon solvents may be overcome by the use of the highly reactive menthyl-lithium, which exchanges rapidly with bromobenzene even in p e n t a n e . -iodostyrene) and n-butyl-lithium in b e n z e n e (cf. ref. 48). 5), but monolithioferrocene can be prepared in excellent yield by metal-halogen exchange between n-butyl-lithium and bromo- or iodo-ferrocene. 2). However, in polyhalogenobenzenes, the inductive effect of neighbouring halogen atoms (together with some steric effect) is sufficient to promote lithium-chlorine exchange, and the resulting lithium compounds are stable enough to be characterised.
314). As might have been predicted, 1-methylimidazole is metallated in the 2-position, between the hetero-atoms. But when the 2-position is blocked, as in the case of 1,2-dimethylimidazole, the 5-position is metallated in preference to the 4-position. ) A similar preference is observed for 1-substituted pyrazoles, which are also metallated in the 5-position. Isothiazole is metallated in the 5-position, adjacent t o sulphur, rather than in the 3-position, adjacent to nitrogen. 1 (200) (188) (188) ( 3 5 6 ) Reactions between organolithium compounds and halogeno-substituted heterocyclic aromatic compounds involve competition between metallation and metal-halogen exchange (see p p .